These Are the Best Bosses in the World (And You Should Be Working for Them)

Odds are you’ve probably had one or two (harmless) visions of strangling your boss.

We get it, stress is a helluva drug.

But that doesn’t mean there aren’t some bosses out there who are doing amazing things for their employees.

Corporate culture, perks, benefits – you name it, and these are the leaders you wish you were following.  

Here’s who’s doing it right…

Greg Dixon: Flight Centre Canada

Flight Centre is repeatedly listed as one of Canada’s top companies to work for. Employee perks include in-house wellness and financial consultants (who advise on everything from healthy choices to the firm’s share plan), a monthly reward system for top teams and individuals, companywide conferences in destinations like Jamaica, and a global gathering for top performers that cuts no corners (last year’s event featured singers will.i.am and Jessie J.) Not to mention, there’s ample room for growth, and the majority (over 90 per cent) of the top dogs began as travel consultants.

Leerom Segal, Peter Cordy, and Aaron Goldstein: Klick Health 

Klick Health’s corporate culture makes anyone jealous. The Klick Concierge regularly orders dinner for any Klickster who works late, manages their on-site health and wellness centre (which offers free daily yoga and fitness classes) a dry cleaning service (right?), and handles customized upon-request tasks for employees. Employees are rewarded for their work with “Klick it Forward” credits, which they can donate to their favourite charities. Klick also sponsors philanthropic trips for employees to build schools in Rwanda and Kenya. Did we mention their holiday gifts? This year, all employees received Apple Watches (once they launch), and past gifts include Sony PS4 game systems, and Apple TV with large flatscreen TVs. Management remains vocal on their ethos to find a way to demonstrate that the status quo is ridiculous, and then create a sense of excitement about crushing the existing standard.

Ellis Jacob: Cineplex

Cineplex’s Ellis Jacob has been recognized as a strong business leader, and was named the “The Most Innovative CEO of the Year” in 2013 by Canadian Business. Known to shun bureaucracy, a few years back, Ellis asked its more than 10,000 employees for their ideas to expand and innovate business, ending up with 500 ideas that were narrowed down to a dozen. In a recent Canadian Business article, he revealed a focus on collaboration and fostering both a family and entrepreneurial environment with its employees that allows them to experiment.

Debbie Cosic: In2ition Realty

There’s no boys’ club or glass ceiling at In2ition Realty, one of Canada’s fastest-growing real estate and marketing firms. It’s owned by Debbie Cosic, run by female management, and – in a culture where women are increasingly expected to do it all – the company culture is tailored to the realities of women’s lives. This means a flexible workspace where a child’s midday doctor’s appointment or 3:30pm pick-up time isn’t frowned upon. Not one to micromanage, she let’s employees work when they want and how they want. Cosic also believes in keeping it in the family; the company’s director of operations started off as a receptionist. Not to mention, she pays better; in an industry where employees are usually reliant solely on commission, her sales agents get a base salary, and can buy into a shared real estate investment fund.

Dietrich Mateschitz: Red Bull

Red Bull CEO Dietrich Mateschitz is known for his over-the-top (and sometimes record-breaking) marketing ideas. The company’s fun, youthful, and anti-authoritarian marketing agenda is also reflected in its corporate culture, and Red Bull employees worldwide are known to enjoy no shortage of perks. Have you seen the Red Bull Toronto office? It looks more like an adventure play land or new-age nightclub than an office, with things like mini fridges full of complimentary Red Bull (naturally), pod shaped conference rooms, a bar/lounge area, and a rooftop patio that’s a dream for events. Though employees are pretty much allowed to make their own hours, who would ever want to leave?

Kirstine Stewart: Twitter Canada

Kirstine Stewart, Managing Director and Head of Twitter Canada, is vocal on the changing nature of leadership in the face of things like the millennials, the boomers, changing values, corporate responsibility, and globalization. At a Women of Influence luncheon last year, she suggested the adaptation of a West Coast mentality of collaboration, both between companies and internally. Stewart is adamant about a sharing of credit and power in the workplace. Huge value is placed on the young people at Twitter, and they look to the opportunities of the different value systems of the millennial, who understand technology and its rapid pace of growth. That’s why Twitter isn’t run by hierarchy, but collaboration. Management hears all voices of employees through a Twitter buzz platform where any employee can comment. And yes, they’re allowed to tweet during meetings. 

Larry Page and Sergey Brin: Google

It’s no surprise that Google has a pretty amazing corporate culture. Management is vocal on the importance of it and giving the company a “family” appeal, offering employees everything from free massages and transportation, to talks with celebrities and other business leaders. Google’s in-house tech support shop, TechStop, offers employees hardware and software guidance 24/7, and the company operates under an 80/20 rule that allows employees to dedicate 80 per cent of their time to their primary role and 20 per cent to creative passion projects that they feel will benefit the company. Like other offices, Google’s Toronto office supplies free, daily health-conscious meals for staff, and features video game stations, foosball tables, and fun décor. 

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